• Title/Summary/Keyword: flavanone

Search Result 91, Processing Time 0.032 seconds

Isolation of Antioxidative Compound from Scutellaria baicalensis G. (황금으로부터 항산화 활성 성분의 분리)

  • Kim, Seok-Chang;Ahn, Kun-Seok;Park, Chae-Kyu;Jeon, Byeong-Seon;Lee, Jong-Tae;Park, Won-Jong
    • Korean Journal of Medicinal Crop Science
    • /
    • v.14 no.4
    • /
    • pp.212-216
    • /
    • 2006
  • Root of Scutellaria baicalensis G. was extracted with methanol and water to give the yield of 30.0% in order to find the antioxidant substance. The extract was fractionated with diethyl ether, n-butanol and water to test the inhibitive activity against xanthine oxidase. Three fractions inhibited the activities of xanthine oxidase by 48.2%, 10.2% and 2.8%, respectively, at the amount of $0.1\;{\mu}g$. A component that exhibited strong inhibition of xanthine oxidase was isolated from diethyl ether fraction (SE Fr.) by silica gel column chromatography and HPLC, and then identified by $^1H-NMR$, $^{13}C-NMR$ and MS spectrophotometry. EDA (Electron Donating ability) of the compound was 28.5% at the concentration $100\;{\mu}g/3\;ml$. That was identified to be 3,5,7-trihydroxy-2'-methoxyflavanone by spectrophotometric analysis using $^1H-NMR,\;^{13}C-NMR$ and Mass spectrophotometry.

Poncirin Inhibits Osteoclast Differentiation and Bone Loss through Down-Regulation of NFATc1 In Vitro and In Vivo

  • Chun, Kwang-Hoon;Jin, Hyun Chul;Kang, Ki Sung;Chang, Tong-Shin;Hwang, Gwi Seo
    • Biomolecules & Therapeutics
    • /
    • v.28 no.4
    • /
    • pp.337-343
    • /
    • 2020
  • Activation of osteoclast and inactivation of osteoblast result in loss of bone mass with bone resorption, leading to the pathological progression of osteoporosis. The receptor activator of NF-κB ligand (RANKL) is a member of the TNF superfamily, and is a key mediator of osteoclast differentiation. A flavanone glycoside isolated from the fruit of Poncirus trifoliata, poncirin has anti-allergic, hypocholesterolemic, anti-inflammatory and anti-platelet activities. The present study investigates the effect of poncirin on osteoclast differentiation of RANKL-stimulated RAW264.7 cells. We observed reduced formation of RANKL-stimulated TRAP-positive multinucleated cells (a morphological feature of osteoclasts) after poncirin exposure. Real-time qPCR analysis showed suppression of the RANKL-mediated induction of key osteoclastogenic molecules such as NFATc1, TRAP, c-Fos, MMP9 and cathepsin K after poncirin treatment. Poncirin also inhibited the RANKL-mediated activation of NF-κB and, notably, JNK, without changes in ERK and p38 expression in RAW264.7 cells. Furthermore, we assessed the in vivo efficacy of poncirin in the lipopolysaccharide (LPS)-induced bone erosion model. Evaluating the micro-CT of femurs revealed that bone erosion in poncirin treated mice was markedly attenuated. Our results indicate that poncirin exerts anti-osteoclastic effects in vitro and in vivo by suppressing osteoclast differentiation. We believe that poncirin is a promising candidate for inflammatory bone loss therapeutics.

Characterization of flavonoids specific gene expression in the petals of Dianthus caryophyllus (carnation) (카네이션 (Dianthus caryophillus)의 색소 발현체계 분석)

  • Hur, Suel-Hye;Ahn, Byung-Joon;Joung, Hyang-Young;Hyung, Nam-In;Min, Byung-Whan
    • Journal of Plant Biotechnology
    • /
    • v.36 no.4
    • /
    • pp.415-422
    • /
    • 2009
  • This study aimed to develop carnation cultivars with new coloring system. We used four genes of Petunia hybrida - chalcone synthase (CHS), flavanone 3-hydroxylase (FHT), dihydroflavonol 4-reductase (DFR), and anthocyanidin synthase (ANS) - as probes, in order to isolate four genes from carnations (Dianthus Caryophyllus). The isolated genes were used as probes in order to select mutants out of collected carnations, using Northern blot analysis. The Northern blot analysis revealed 10 DFR mutants - Gumbyul, Eunbyul, Ballatyne, Crystal, Eugenia, Koreno, Imp. White Sim, West Crystal, White Alpine, and White Charotte. Six among the selected 10 cultivarswere excluded from the target cultivars, because Eugenia, Imp. White Sim, and White Alpine were proved to be double mutants of DFR and ANS, Koreno was considered to be a double mutant of DFR and CHS, and Gumbyul and Ballatyne were proved to be double mutants of DFR and CHI (Chalcone isomerase). Consequently, we selected five DFR mutants, including Virginie, which was already selected as a DFR mutant. Finally, we measured DFR activities in order to confirm the selection, and the results showed that all of the five cultivars - Eunbyul, Crystal, West Crystal, White Charotte, and Virginie - had got no DFR activity.

Constituents of Flowers of Carthamus tinctorius L. and Their Antioxidant Activity (홍화의 성분 분리 및 항산화 활성)

  • Choi, Hyun-Gyu;Jiang, Yan-Fu;Park, Sung-Hee;Son, Ae-Ryang;Na, Min-Kyun;Lee, Seung-Ho
    • Korean Journal of Pharmacognosy
    • /
    • v.42 no.2
    • /
    • pp.110-116
    • /
    • 2011
  • As part of our ongoing study focused on the discovery of antioxidants from natural products by measuring the DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity, methanol extract of flowers of Carthamus tinctorius L. was found to show potent antioxidant activity. Activity-guided fractionation of the methanol extract lead to the isolation of twenty compounds including two flavonol glycosides, quercertin-3-O-${\beta}$-D-glucopyranoside (12) and kaempferol-3-O-${\alpha}$-L-rhamnopyranosyl-${\beta}$-D-glucopyranoside (18), two flavanone glycosides, (2S)-4',5,6,7-tetrahydroxyflavanone 6-O-${\beta}$-D-glucopyranoside (15) and (2R)-5,7,8',4-tetrahydroxyflavanone 8-O-${\beta}$-D-glucopyranoside (16), and two acetylenic glycosides, 8Z-decaene-4,6-diyne-1-O-${\beta}$-D-glucopyranoside (13) and 4,6-decadiyne-1-O-${\beta}$-D-glucopyranoside (14). Their chemical structures were identified by using spectroscopic analysis. Among them, compounds 12-18 were tested in DPPH assay. Compounds 13-16 were first reported to their antioxidant activity. Quercertin-3-O-${\beta}$-D-glucopyranoside (12) showed the most potent inhibitory effect on DPPH with $IC_{50}$ value of 56.7 ${\mu}M$.

Extractives of the Wood of Black Locust and the Bark of Poplar as Decay-Resistant Hardwood Tree Species (내후성 활엽수종인 아까시나무 목질부와 현사시나무 수피의 추출성분)

  • Bae, Young-Soo;Ham, Yeon-Ho
    • Journal of the Korean Wood Science and Technology
    • /
    • v.28 no.3
    • /
    • pp.52-61
    • /
    • 2000
  • Black locust(Robinia pseudoacacia) and poplar(Populus alba ${\times}$ glandulosa) trees were collected, extracted with acetone-$H_2O$(7:3, v/v) after drying, fractionated with hexane, chloroform and ethylacetate, and freeze dried to get some brown powder. Each fraction of the powder was chromatographed on a Sephadex LH-20 column using a series of aqueous methanol and ethanol-hexane mixture as eluting solvents. The wood extractives of black locust contained (+)-leucorobinetinidin as flavan, robtin as flavanone and dihydrorobinetin as flavanonol, and robinetin as flavonol. The poplar bark extractives contained various kinds of phenolic compounds : (+)-catechin as flavan, naringeoin, eriodictyol, sakuranetin, aromadendrin and taxifolin as flavanonol, salireposide as salicin derivative, and minor compounds such as aesculin and p-coumaric acid. However, aesculin has not been reported as a constituent of the poplar bark in Korea yet. NMR and FAB-MS analyses were done to elucidate the structures of isolated phenolic constituents.

  • PDF

Antioxidantive Effectiveness of Trichosanthes kirilowii Maximowicz Extracts (하늘타리(Trichosantes kirilowii Maximowicz)추출물의 항산화 효과)

  • Zhoh, Choon Koo;Uhm, Tae Yong;Kim, Joo Chan
    • Applied Chemistry for Engineering
    • /
    • v.18 no.6
    • /
    • pp.625-629
    • /
    • 2007
  • Recently, there is a growing interest about unsaturated lecithin having excellent characteristics of skin affinity and absorbency. Accordingly, this study intended to develop a natural sulfuration material in order to enhance the stability of oxidation of unsaturated lecithin and substitute existing sulfuration materials which indicate variability and toxicity. As sulfuration components, plenol acid family, 3,5-dihydroxybenzoic acid, and flavanone were analyzed. Total polyphenol content was higher in the root extracts (133.85 mg/g) than in the fruit extracts (53.5 mg/g). Above 100 ppm polyphenol content, the free radical removal efficiency and lipid oxidation prevention of the root extracts were 20.1 and 19.2% superior compared with BHT respectively. Also, the extracts indicated high survival rate of more than 95% below 1250 ppm, showing the stability. For the stability of liposome made from an unsaturated lecithin, the root extracts were superior to the fruit extracts. Especially, 15.1 and 13.9% of sulfuration effect and zeta potential were improved with 9.3% reduced particle size compared with BHT as the control group, respectively.

Inhibitory Effects of Naringenin and Its Novel Derivatives on Hyaluronidase

  • Moon, Sun-Hee;Kim, Kee-Tae;Lee, Na-Kyoung;Han, Ye-Sun;Nah, Seung-Yeol;Cho, Ssang-Goo;Park, Yong-Sun;Paik, Hyun-Dong
    • Food Science and Biotechnology
    • /
    • v.18 no.1
    • /
    • pp.267-270
    • /
    • 2009
  • Naringenin is a bioactive flavanone containing antioxidative, anti-inflammatory, and anticarcinogenic properties. The inhibitory effects on hyaluronidase of naringenin and its novel derivatives were evaluated. Among these flavonoids at $200{\mu}M$ concentration, 7-O-butyl naringenin had the highest inhibitory effect on hyaluronidase with 44.84%. In addition, For naringenin at concentrations of 0, 150, and $190{\mu}M$, the apparent Michaelis constants ($_{app}K_m$) were calculated to be $0.60{\pm}0.02$, $0.43{\pm}0.02$, and $0.41{\pm}0.01\;mg/mL$ of substrate, respectively; for 7-O-butyl naringenin at 0, 20, and $30{\mu}M$ concentrations, those were $0.44{\pm}0.03$ and $0.27{\pm}0.03\;mg/mL$, respectively. The $V_{max}$ values at 150 and $190{\mu}M$ naringenin were $0.59{\pm}0.02$ and $0.56{\pm}0.01\;mg/mL/min$, respectively; and those at 20 and $30{\mu}M$ 7-O-butyl naringenin were $0.50{\pm}0.02$ and $0.33{\pm}0.02\;mg/mL/min$, respectively. However, the slopes of each inhibitory reaction were not significantly different. Therefore, naringenin and 7-O-butyl naringenin were shown to be uncompetitive inhibitors. These results demonstrate the potential use of 7-O-butyl naringenin as an anti-inflammatory substance.

Polymorphism and Expression of Isoflavone Synthase Genes from Soybean Cultivars

  • Kim, Hyo-Kyoung;Jang, Yun-Hee;Baek, Il-Sun;Lee, Jeong-Hwan;Park, Min Joo;Chung, Young-Soo;Chung, Jong-Il;Kim, Jeong-Kook
    • Molecules and Cells
    • /
    • v.19 no.1
    • /
    • pp.67-73
    • /
    • 2005
  • Isoflavones are synthesized by isoflavone synthases via the phenylpropanoid pathway in legumes. We have cloned two isoflavone synthase genes, IFS1 and IFS2, from a total of 18 soybean cultivars. The amino acid residues of the proteins that differed between cultivars were dispersed over the entire coding region. However, amino acid sequence variation did not occur in conserved domains such as the ERR triad region, except that one conserved amino acid was changed in the IFS2 protein of the GS12 cultivar ($R_{374}G$) and the IFS1 proteins of the 99M06 and Soja99s65 cultivars ($A_{109}T$, $F_{105}I$). In three cultivars (99M06, 99M116, and Simheukpi), most of amino acid changes were such that the difference between the amino acid sequences of IFS1 and IFS2 was reduced. The expression profiles of three enzymes that convert naringenin to the isoflavone, genistein, chalcone isomerase (CHI), isoflavone synthase (IFS) and flavanone 3-hydroxylase (F3H) were examined. In general, IFS mRNA was more abundant in etiolated seedlings than mature plants whereas the levels of CHI and F3H mRNAs were similar in the two stages. During seed development, IFS was expressed a little later than CHI and F3H but expression of these three genes was barely detectable, if at all, during later seed hardening. In addition, we found that the levels of CHI, F3H, and IFS mRNAs were under circadian control. We also showed that IFS was induced by wounding and by application of methyl jasmonate to etiolated soybean seedlings.

Effect of Ponciri Fructus Extracts Fermented with Ganoderma lucidum on the Collagen Synthesis and Expression of Matrix Metalloproteinase-1 (콜라겐 합성과 MMP-1 발현에 대한 생물전환 지실 추출물의 효과)

  • Lee, Gye Won;Park, Sung Min;Yoo, Yung Choon;Cho, Young Ho
    • KSBB Journal
    • /
    • v.28 no.2
    • /
    • pp.106-114
    • /
    • 2013
  • Ponciri fructus, the unripe fruits of Poncirus trifoliata, are widely used in oriental traditional medicine as a remedy for inflammation, gastritis, emesis, digestive ulcers, allergy, and dysentery. To study the anti-wrinkle effects of Ponciri fructus extract (PFE) containing flavanone glycosides, PFE was fermented with Ganoderma lucidum mycelia and its biological activities were investigated. In Ponciri fructus extracts fermented with G. lucidum (G-PFE), polyphenol content was $1,021.00{\pm}0.50{\mu}g/mL$ and flavonoid content was $589.41{\pm}0.21{\mu}g/mL$. G-PFE was found to scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals and superoxide anion radical by a dose dependent manner, respectively. G-PFE showed higher antioxidant activity than that of PFE. In addition, the photoprotective properties of G-PFE was tested in human dermal fibroblasts (HDF) exposed to UVA radiation. G-PFE inhibited the activity of matrix metalloproteinase-1 (MMP-1) and showed a dose dependent decrease in the expression level of MMP-1. G-PFE also increased collagen biosynthesis in HDF. These results demonstrate that G-PFE could be useful as a potential cosmetic ingredient for anti-wrinkle.

Isolation and Identification of Antioxidants from Peanut Shells and the Relationship between Structure and Antioxidant Activity

  • Wee, Ji-Hyang;Moon, Jae-Hak;Eun, Jong-Bang;Chung, Jin-Ho;Kim, Young-Gook;Park, Keun-Hyung
    • Food Science and Biotechnology
    • /
    • v.16 no.1
    • /
    • pp.116-122
    • /
    • 2007
  • Four compounds with antioxidant activity were isolated from the MeOH extract of peanut shells (pod) and identified as 5,7-dihydroxychromone (1), eriodictyol (2), 3',4',7-trihydroxyflavanone (3), and luteolin (4) by electron impact-mass spectrometry (EI-MS) and nuclear magnetic resonance (NMR) analyses. The relationship between antioxidant activity and chemical structure of the isolated compounds with their analogues [(-)-epicatechin, quercetin, taxifolin] was examined by measuring 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity and using the 2-deoxy-D-ribose degradation system. The order of antioxidant activity on the basis of DPPH radical-scavenging was quercetin = (-)-epicatechin (6.0 molecules) > taxifolin (4,5 molecules) > 4 (luteolin; 4.0 molecules) > 2 (eriodictyol; 2.5 molecules) > 3 (3',4',7-trihydroxy-flavanone; 2.0 molecules) > 1 (5,7-dihydroxychromone; 0.5 molecules). On the other hand, using the 2-deoxy-D-ribose degradation system, the order of antioxidant activity was quercetin > 4 >> (-)-epicatechin ${\geq}\;2\;{\geq}$ taxifolin > 3 > 1. These compounds from peanut shells may provide defensive measures against oxidative stress and insects in the soil.